Water → HCID 21888022, compound

HRID 719820Notes

Reaction equation

HRID 719820 reaction equation
[C:1]([Cl:4])(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][N:14]([CH3:32])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([C:21]1[CH:31]=[CH:30][C:24]2[CH2:25][CH2:26][NH:27][CH2:28][CH2:29][C:23]=2[CH:22]=1)=[O:20].C(N(CC)CC)C.O>O1CCCC1>[ClH:4].[C:1]([N:27]1[CH2:26][CH2:25][C:24]2[CH:30]=[CH:31][C:21]([C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH2:13][CH2:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[Cl:5])[CH3:32])=[CH:22][C:23]=2[CH2:29][CH2:28]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58737268HCID 58737268, compound

Product 1

HCID 21888022HCID 21888022, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (54 μl) was added to a solution of 5-[[2-(2-chlorophenyl)ethyl](methyl)amino]-1-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1-pentanone (294 mg) obtained in Example 205 and triethylamine (13911) in tetrahydrofuran (2 ml). After stirring at room temperature for 60 minutes, water (10 g) was added, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and purified by silica gel column chromatography to give a free base compound of the title compound as a pale yellow oil (280 mg). A solution of the free base compound in ethanol was treated with hydrogen chloride (ethyl acetate solution) to give the title compound as pale yellow amorphous powders (220 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-4fd64d19122d401686aef854224f965d
Source dataset
uspto-grants-2006_11
Patent number
US07132547B2

Reaction notes

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